RUI: Synthesis of Highly Functionalized N-Alkyl 2-Pyridones and Their Analogues

Calvin University, Grand Rapids MI

Investigators

Abstract

In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Carolyn Anderson of the Department of Chemistry and Biochemistry at Calvin College will explore the development of facile methods for the synthesis of structures containing N-alkyl pyridones and their further transformation into targets of importance. These targets include a unique class of amino acid homologues, which will subsequently be used to expand our understanding of the helical structure of peptides containing these subunits. The development of asymmetric variants of these methods will also be pursued. These methods are based on the conversion of readily available 2-alkoxypyridine substrates. This work could lead to a suite of chiral and achiral methods for preparing highly functionalized N-alkyl 2-pyridones. Such chemistry will make these and their related analogues available to the broader chemical community. In addition, basic knowledge related to asymmetric gold(III) catalysis is also expected to be garnered during these studies. Successful development of these methodologies and targets will have an impact on the synthetic community as well as those involved in the development of organic materials, medicinal leads, and asymmetric transformations. In addition, these efforts will provide excellent training for undergraduate research collaborators and an opportunity for pre-college students, especially those from historically underrepresented groups, to gain hands-on experience in the chemistry laboratory.